One of the missions of OB/LW is to attract new learners, and it's clear that they are succeeding. But the format feels like a very difficult one for those new to these ideas, with beginner-level ideas interspersed with advanced or unsettled theory and meta-level discussions. You wouldn't play <insert cool-sounding, anime-ish video game here> with the levels on shuffle mode, but reading Less Wrong must feel like doing so for initiates.
How do we make the site better for learners? Provide a "syllabus" that shows a series of OB and LW posts which should be read in order? Have a separate beginner site or feed or header? Put labels on posts that designate them with a level?
Ordering by average perceived difficulty won't solve the problem as different new readers will have very different backgrounds - one might find mathy post A easy and psychology post B impenetrable, while the next guy votes the opposite.
Maybe posters could be encouraged to watch out for illusion of transparency and clearly signpost to the next step back on the inferential distance tree, and commenters to suggest such links where the posters forget. I could always figure out what OB posts were about by following these links (whether to other OB posts or not) as far down as needed until I could understand the top post.